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Our top choices for Winston holiday rentals

Refined Modern Alpine Cabin / Private Mountain Retreat for 4

Refined Modern Alpine Cabin / Private Mountain Retreat for 4
Townsend
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and a true escape into the heart of Montana. What a wonderful place for us to celebrate our 30th anniversary. Thank you!!!!"
United States
Sheila E.
The price is £287
includes taxes & fees
21 Feb - 22 Feb
Refined Modern Alpine Cabin / Private Mountain Retreat for 4

Refined Modern Alpine Silos Cabin on 1,500 Private Acres/Mountain Retreat for 4

Refined Modern Alpine Silos Cabin on 1,500 Private Acres/Mountain Retreat for 4
Townsend
10.0 out of 10, Exceptional, (1 review)
"Location awesome and clean cabin "
United States
Meghan J.
The price is £296
includes taxes & fees
21 Feb - 22 Feb
Refined Modern Alpine Silos Cabin on 1,500 Private Acres/Mountain Retreat for 4

Great place to crash after a Montana adventure!

Great place to crash after a Montana adventure!
East Helena
8.0 out of 10, Very good, (1 review)
"Clean quiet space. "
United States
Addy C.
The price is £75
includes taxes & fees
1 Mar - 2 Mar
Great place to crash after a Montana adventure!

Cozy cabin nestled beside a spring-fed pond&hobby farm in the Elkhorn Mountains

Cozy cabin nestled beside a spring-fed pond&hobby farm in the Elkhorn Mountains
East Helena
10.0 out of 10, Exceptional, (21 reviews)
"Very cute cabin and property. Enjoyed our time."
United States
Amanda F.
The price is £291
includes taxes & fees
21 Feb - 22 Feb
Cozy cabin nestled beside a spring-fed pond&hobby farm in the Elkhorn Mountains

Cabin 22 - The Movie Cabin

Cabin 22 - The Movie Cabin
Helena
8.8 out of 10, Excellent, (3 reviews)
"Nice affordable place"
United States
Jackie L.
The price is £75
includes taxes & fees
23 Feb - 24 Feb
Cabin 22 - The Movie Cabin

Cozy townhouse close to Hospital & Capital

Cozy townhouse close to Hospital & Capital
Helena
10.0 out of 10, Exceptional, (98 reviews)
"Perfect stay!"
United States
Craig R.
The price is £155
includes taxes & fees
25 Feb - 26 Feb
Cozy townhouse close to Hospital & Capital

Suite 35 - Victorian Suite W/ Porch

Suite 35 - Victorian Suite W/ Porch
Helena
8.0 out of 10, Very good, (2 reviews)
"Stayed here twice after picking up each of our 2 boxer puppies in Bozeman on our way back to Kalispell. Wonderful area with beautiful historic houses."
United States
Andrea R.
The price is £75
includes taxes & fees
23 Feb - 24 Feb
Suite 35 - Victorian Suite W/ Porch

Suite 32 - King Suite

Suite 32 - King Suite
Helena
9.8 out of 10, Exceptional, (16 reviews)
"Nice place to stay that avoids the hotel vibe."
United States
Erik
The price is £75
includes taxes & fees
22 Feb - 23 Feb
Suite 32 - King Suite

Cabin 26 - Coyboy Corner

Cabin 26 - Coyboy Corner
Helena
8.0 out of 10, Very good, (1 review)
"Nice place would recommend. The only thing i wish they had was a better outside place to sit, maybe a patio set some where."
United States
Mark C.
The price is £91
includes taxes & fees
10 Mar - 11 Mar
Cabin 26 - Coyboy Corner

Spacious artist's studio loft apartment with view

Spacious artist's studio loft apartment with view
Helena
9.8 out of 10, Exceptional, (8 reviews)
"We enjoyed this "
United States
Mary L.
Spacious artist's studio loft apartment with view

Lee's apartment building on saddle mountain

Lee's apartment building on saddle mountain
Clancy
10.0 out of 10, Exceptional, (64 reviews)
"So much thoughtful care was put into creating this bunkhouse retreat. We especially loved the friendly dogs that greeted us in the morning."
United States
Audrey H.
The price is £171
includes taxes & fees
27 Feb - 28 Feb
Lee's apartment building on saddle mountain

Suite 33 - Queen Suite W/ Walk-In Shower

Suite 33 - Queen Suite W/ Walk-In Shower
Helena
9.8 out of 10, Exceptional, (7 reviews)
"This place is pretty great, and had been remodeled nicely. Perfect for a few days!"
United States
Jessica B.
The price is £91
includes taxes & fees
8 Mar - 9 Mar
Suite 33 - Queen Suite W/ Walk-In Shower

Cabin 23 - Hunters Haven

Cabin 23 - Hunters Haven
Helena
8.0 out of 10, Very good, (1 review)
"Not fancy, but comfortable, which fits me perfectly. Heater worked well, comfy bed, cute decor. Easy access."
United States
Christopher
The price is £75
includes taxes & fees
22 Feb - 23 Feb
Cabin 23 - Hunters Haven

Helena Townhouse next to Skelton Park (Dog and kid friendly)

Helena Townhouse next to Skelton Park (Dog and kid friendly)
Helena
10.0 out of 10, Exceptional, (61 reviews)
"Nice property, great price, great location "
United States
Joan J.
The price is £133
includes taxes & fees
25 Feb - 26 Feb
Helena Townhouse next to Skelton Park (Dog and kid friendly)

Suite 30 - Double Queen Corner Suite

Suite 30 - Double Queen Corner Suite
Helena
9.2 out of 10, Wonderful, (7 reviews)
"Perfect location and easily accessible."
United States
Shayna B.
The price is £75
includes taxes & fees
24 Feb - 25 Feb
Suite 30 - Double Queen Corner Suite

Suite 34- Victorian Suite

Suite 34- Victorian Suite
Helena
7.4 out of 10, Good, (6 reviews)
"Safe, clean, had everything we needed! Conveniently located. "
United States
Melonie W.
The price is £91
includes taxes & fees
1 Mar - 2 Mar
Suite 34- Victorian Suite

Cabin 25 - The Ski Lodge

Cabin 25 - The Ski Lodge
Helena
8.8 out of 10, Excellent, (6 reviews)
"Location and friendliness"
United States
Isidor R.
The price is £91
includes taxes & fees
1 Mar - 2 Mar
Cabin 25 - The Ski Lodge

Cabin 21 - Bicycle Retreat

Cabin 21 - Bicycle Retreat
Helena
10.0 out of 10, Exceptional, (1 review)
"Easy check in, good communications, good price"
United States
Jackie L.
The price is £75
includes taxes & fees
23 Feb - 24 Feb
Cabin 21 - Bicycle Retreat

Suites 35 +Up - Victorian Queen

Suites 35 +Up - Victorian Queen
Helena
9.4 out of 10, Exceptional, (9 reviews)
"Thank you for a great stay- the location was perfect as we were in town for the governors cup race. Enjoyed my morning coffee in the sunroom. Comfy beds & plenty of pillows & towels. "
United States
Tiffany K.
The price is £91
includes taxes & fees
1 Mar - 2 Mar
Suites 35 +Up - Victorian Queen

Suite 31 - Private Porch Suite

Suite 31 - Private Porch Suite
Helena
9.6 out of 10, Exceptional, (7 reviews)
"Great stayEasy check in and clean and comfortable place to stay. Close to great restaurants and a great park"
United States
Monica C.
The price is £91
includes taxes & fees
22 Feb - 23 Feb
Suite 31 - Private Porch Suite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Winston Hotel Reviews

Find out more about Winston

Everything you need to know about Winston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winston holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winston. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winston holiday rentals we have selected for you start as low as £102 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winston holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Winston?

Yes, there are holiday rentals close to the most popular sights in Winston, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winston has to offer?

Cozy townhouse close to Hospital & Capital: This holiday home rental outside of Winston offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Winston?

Canyon Ferry Lake and Missouri River are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Canyon Ferry Wildlife Management Area and Montana State Capitol.

What are holiday rentals like in Winston?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winston. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a small group gathering.